Hydrochloric Acid → 1,3-Dipropyl-8-(6-chloro-3-pyridyl)xanthine

HRID 2105171Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][N:3]=1.[NH2:11][C:12]1[C:13](=[O:26])[N:14]([CH2:23][CH2:24][CH3:25])[C:15](=[O:22])[N:16]([CH2:19][CH2:20][CH3:21])[C:17]=1[NH2:18].O.Cl>C(Cl)Cl.N1C=CC=CC=1.[OH-].[Na+]>[CH2:23]([N:14]1[C:13](=[O:26])[C:12]2[NH:11][C:6]([C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[N:18][C:17]=2[N:16]([CH2:19][CH2:20][CH3:21])[C:15]1=[O:22])[CH2:24][CH3:25]

Participants

Conditions

Temperature: 5 °C

Procedure

6-Chloronicotinoyl chloride (1.83 g, 10.4 mmol), in CH2Cl2 (20 ml) was added dropwise to a solution of 5,6-diamino-1,3-dipropyluracil (1.808 g, 8 mmol) in dry pyridine (8.2 ml) maintained at 5° C. The reaction was warmed to room temperature and stirred for an additional 3 hours. Water (50 ml) was added to quench the reaction. The solvent was evaporated to afford a dark colored oil. The oil was refluxed for 2 h in 2N NaOH (20 ml). After cooling, the pH was carefully adjusted to 7 with concentrated HCl. A solid formed and was collected and washed with water (20 ml), ether (20 ml) and chloroform(20 ml) to provide an off-white solid (1.9 g). The product was used in the next step without further purification.

Workup

temperatureThe reaction was warmed to room temperature
customto quench
customthe reaction
customThe solvent was evaporated
customto afford a dark colored oil
temperatureAfter cooling
customA solid formed
customwas collected
washwashed with water (20 ml), ether (20 ml) and chloroform(20 ml)

Sources & evidence

ORD record: ord-1dde7c92ca6f429ebead756dadb8c4db
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579348B2

Reaction notes

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